1-Methylpiperazine → HCID 66558672, compound

HRID 1530539Notes

Reaction equation

HRID 1530539 reaction equation
CS(O[CH:6]([C:8]1[CH:21]=[C:20]2[C:11]([O:12][CH2:13][CH2:14][N:15]3[C:19]2=[N:18][C:17]([C:22]2[N:26]([CH:27]([CH3:29])[CH3:28])[N:25]=[CH:24][N:23]=2)=[CH:16]3)=[CH:10][CH:9]=1)[CH3:7])(=O)=O.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[CH:27]([N:26]1[C:22]([C:17]2[N:18]=[C:19]3[C:20]4[CH:21]=[C:8]([CH:6]([N:34]5[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]5)[CH3:7])[CH:9]=[CH:10][C:11]=4[O:12][CH2:13][CH2:14][N:15]3[CH:16]=2)=[N:23][CH:24]=[N:25]1)([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 86671465HCID 86671465, compound

Product 1

HCID 66558672HCID 66558672, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethyl methanesulfonate (246 mg, 0.590 mmol) in 1-methylpiperazine (25 mL) was heated at 90° C. for 16 h. The solvent was removed and the residue was purified by Combi-flash eluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3 to give 146. Separation of the enantiomers and further purification by chiral HPLC (AY-H column, 5% EtOH isocratic) gave: 44.3 mg of one enantiomer and 40.0 mg of the other (34% total yield).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by Combi-flash
  3. washeluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-7878e55b6b02451586a7da07d8066027
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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